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Method of manufacturing fatty acid ethyl esters from triglycerides and alcohols

a technology of triglycerides and alcohols, which is applied in the direction of fatty acid chemical modification, fatty oil/acid recovery from waste, fatty oil/fat refining, etc., can solve the problems of putting a strain on the transformation cost and all these specifications are not always useful

Inactive Publication Date: 2010-12-14
INST FR DU PETROLE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent describes a way to make a mixture of fatty acid esters and glycerin from vegetable or animal oils using two stages with methanol and ethanol. This process is cost-effective and can produce high-purity fatty acid ethyl esters.

Problems solved by technology

In the case of heating oil, it is obvious that all these specifications are not always useful and even sometimes detrimental but, the heating oil market and the gas oil market being often confused, the heating oil specifications resemble the gas oil specifications because, in France, heating oil can be used in agricultural tractors and building engines.
In short, most commercial ester manufacturing methods quite readily lead to raw products (esters and glycerin) that however have to be purified in depth by means of various treatments that eventually put a strain on the transformation cost.

Method used

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  • Method of manufacturing fatty acid ethyl esters from triglycerides and alcohols
  • Method of manufacturing fatty acid ethyl esters from triglycerides and alcohols
  • Method of manufacturing fatty acid ethyl esters from triglycerides and alcohols

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0061]100 g colza oil and 100 g ethanol are fed at 200° C. and at a LHSV of 0.25 h−1 (volume of oil per volume of catalyst and per hour) into a fixed-bed reactor containing 110 ml of a catalyst consisting of a mixed zinc aluminate oxide.

[0062]After a residence time of about 110 minutes, a mixture consisting of about 93.2% by mass of ethyl esters, 3.7% by mass of monoglycerides, the 100% complement being made up of triglycerides, diglycerides, sterols and sterol esters, is obtained. This composition is not compatible with the specifications required by the EN 14214 standard for use of this product as a fuel, at least as regards the proportions of esters and of monoglycerides. The reaction therefore has to be continued to improve the conversion.

[0063]To carry out a second catalysis stage, it is necessary to remove all or part of the glycerin formed during the first stage in order to shift the reaction equilibrium. An excess ethanol flash is readily obtained by expansion by going from ...

example 2

According to the Invention

[0066]This example describes the operating conditions of the method involving a first transesterification stage wherein the alcohol used is methanol and a second stage wherein the alcohol used is ethanol. The flowsheet is given in FIG. 2.

[0067]As in example 1, 100 g colza oil and this time 100 g methanol are fed into a fixed-bed reactor containing 110 ml of the same catalyst, at 200° C., at a LHSV of 0.5 h−1 (volume of oil per volume of catalyst and per hour), i.e. a reaction time of 55 minutes. The composition of the reaction mixture at the end of this reaction time is of the order of 93.9% by mass of methyl esters and 3.4% by mass of monoglycerides, the 100% complement consisting of residual triglycerides, diglycerides, sterols and sterol esters.

[0068]The next stage consists in removing all of the excess methanol, in decanting the glycerin formed, then in continuing the operation by means of a second reaction stage wherein the ester phase is fed with etha...

example 3

Comparative

[0073]25 g colza oil, 25 g ethanol and 1 g of the catalyst described in example 1 are fed into a 100-ml autoclave reactor equipped with a stirring system and with a temperature and pressure control device. The medium is brought to 200° C. under stirring. The pressure reaches 32 bar (3.2 MPa).

[0074]A sample is taken from the liquid phase after a 7-hour reaction. After ethanol filtration and evaporation, the medium is allowed to settle. No phase separation is observed, which indicates a negligible free glycerol formation. The ethyl ester concentration is determined by steric exclusion chromatography. It is 23.8% by mass.

[0075]At this stage, 20 g of the product obtained above, 20 g ethanol and 1 g of the catalyst described in example 1 are fed into a 100-ml autoclave reactor equipped with a stirring system and with a temperature and pressure control device. The medium is brought to 200° C. under stirring. The pressure reaches 32 bar (3.2 MPa).

[0076]A sample is taken from the...

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Abstract

A method of manufacturing an ester composition comprising ethyl esters of linear monocarboxylic acids having 6 to 26 carbon atoms from a vegetable or an animal oil, neutral or acid, virgin or recycled, the method comprising: a stage 1 of reaction of vegetable or animal oil with methanol, in the presence of a heterogeneous catalyst comprising a combination of at least one metallic oxide and alumina or a combination of at least two metallic oxides and possibly alumina, and a stage 2 of reaction of the product from stage 1 with ethanol in the presence of a heterogeneous catalyst as defined for stage 1, so as to obtain from vegetable or animal oils, a mixture of fatty acid esters rich in fatty acid ethyl esters and a glycerin of high purity.

Description

FIELD OF THE INVENTION[0001]The present invention relates to the manufacture of monocarboxylic acid ethyl esters from vegetable or animal oils.[0002]It more particularly relates to a new method of producing ethyl esters of linear monocarboxylic acids having 6 to 26 carbon atoms by means of a succession of two stages.BACKGROUND OF THE INVENTION[0003]Esters of fatty substances are currently used in many applications as diesel fuel, heating oil, ecological solvents, base compounds for the manufacture of fatty acid sulfonates, amides, ester dimers, etc.[0004]In the case of diesel fuel, which is today a major application of fatty substance esters, a certain number of specifications were established whose list, limits and methods belong to the EN 14214 (2003) standard currently applicable in Europe. The ester must contain at least 96.5% by mass of esters, at most 0.8% by mass of monoglycerides, at most 0.2% by mass of diglycerides and at most 0.2% by mass of triglycerides, few free fatty ...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C11C3/00C10L1/18
CPCC07C67/03C11C3/003Y02E50/10C07C69/24C07C69/52
Inventor HILLION, GÉRARDDELFORT, BRUNO
Owner INST FR DU PETROLE
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